Manufacture of mercuri-mononitro-ortho-cresol and its salts



tro-will not combine therewith.

Patented May 24,1927. I 1,630,072

UNITED STATES PATENT OFFICE.

GEORGE W. RAIZISS, OF PHILADELPHIA, PENNSYLVANIA, ASSIGNOR TO THE ABBOTT LABORATORIES, OF CHICAGO, ILLINOIS, ACORPORATION OF ILLINOIS.

MANUFACTURE OF MEROURI-MONONITRO-ORTHO-CRESOL AND ITS SALTS.

No Drawing. Application filed May 25, 1923. Serial No. 641,502.

The object of my. invention is to produce grams of the mono 3-nitro ortho-cresol are a mercury derivative of nitro-ortho-cresol, dissolved in 100 c. c. of boiling water, to including the salts of such a derivative; and which is then added 10.2 grams of mercuric which, having succeeded in obtaining it, I acetate dissolved in 50 c. c. of water with the 5 have found to possess superior germicidal addition of 3 to 5 drops of glacial acetic acid. 60 properties and hence having valuable thera- After boiling for about 15 minutes, there is peutic effects when such a remedy is indiadded a solution of sodium hydroxide, sufcated, f cient to leave a slight acidity. A forma- In the beginning of my'researches d xtlon of yellow or stals begins as the result periments t th t, d I f d th t i t. of the reaction. The solution is then boiled 65 t ting t o bi mercuric t t ith for about 4'hours, then cooled, filtered, and the nitro derivative of ortho cresol, the rethe crys alline product after washing, with action desired would not take place with the water, methy1 alcohol and ether, is then dinitro derivative of ortho cresol, but only dried 1nvacuo over concentrated sulfuric u with the mono-nitro, and that therewere no acld- 1 18 pr duct is yellow in color; 70 satisfactorily known methods of obtaining Soluble n s dlum hydroxide; sparingly the latter in pure form. When the mono- Soluble 1 1 0}: Water, oes not melt at nitro derivative is contaminated with the but W (189011113056 at this emperadinitro derivative, mercuric acetate will not l The f lqw ng Structural formula 20 combine. I therefore worked out the followwould represent 7 ing satisfactory method for such purpose, and it forms the first step of my new process, as also the basic constituent of my new compound. A. given quantity of ortho cresol is nitrated by dissolving it in acetic acid, and adding to the solution nitric acid, dissolved in acetic acid, at a very low temperature, below 0C. After the reaction 1s complete the A water soluble derivative of this commixture is diluted with water and permitted pound may b d b u di a (luauto stand overnight at ordmary temperature. tity of it in hot water to which sodium Any free nitric acld then found to be present hydroxide is added until dissolved. The soh u r 1 then dr1ven out b p lution is then concentrated, and cooled, sufmg I Pl Stream of a ee t Tough ficiently to show beginning of crystal formathe mixture. Then steam is mJe and tion. Cooling is then continued until-cryse p mono-Intro compound comes over tallization is complete. These appear as with the steam vapors, and as there is a convery minute crystals. in the form of 'long h h h y dul'mg P of Steam prisms, when examined under a microscope dlstlllatloh to form the dlmhro y, P Q and are reddish brown in color. This water should be taken and examlhed P soluble derivative of my new compound last h yh every half hour duhmg the above described is soluble in hot water and tlllatlohf P 'Q two hodles f 'fi y in methyl alcohol 'and insoluble in ether, cljystallme formatloh, and W111 gand is chemically the sodium salt of l-oxymzed; the P mono ,mtro f y W111 1n mercuri-3-nitro-2-cresol. It has the followthe form of regular prisms, while the dimtro ing .tmctuml formula; com ound will a pear as long'needles' T e former on y can be successfully used in forming a combination with mercuric acetate, at the latter-the impure or dini- In proceedin to make my new ultimate compound, whic may be characterized as an acetoxymercuri-mono nitro ortho-cresol, the following example for producing the mono It will be observed that the example of 55 mercuric derivative may be given. Five my new compound results from combining mula which crystallizes in long prisms, is reddish brown in color, soluble in hot Water and in methyl alcohol and insoluble in ether.

2. The process, which comprises boiling an aqueous solution of 'mono-nitro-orthocresol with an aqueous solution of mercuric acetate acidulated with acetic acid.

3. The process, which comprises reacting on ortho-nitro-cresol with mercuric acetate,

and precipitating acet-oxy-mercuri-nitroortho-cresol by an aqueous solution of an alkali metal hydroxide.

4. The process, which comprises reacting on ortho-nitro-cresol with mercuric acetate, and precipitating acet-oxy-mercuri-nitroortho-cresol by an aqueous solution of an alkali metal hydroxide, dissolving the resulting crystalline product in a hot aqueous solution of alkali-metal-hydroxide and cooling the solution to-separate the alkali-metah hydroxy-mercuri-mono-nitro-ortho cresol.

5. The process, which consists in preparing a boiling water solution of mono nitroortho-cresol, adding thereto an aqueous solution of mercuric acetate and glacial acetic acid, boiling the mixture and adding a solution of sodium hydroxide to leave slight acidity, then crystallizing and separating the resultant product.

In testimony whereof, I have hereunto aflixed my signature this 11th day of May GEORGE W. RAIZISS. 

